In 1616 he completed his mansion of Chilham Castle, Kent.
He was also a "Virginia adventurer," an investor who ventured his capital in the Virginia Company of London. He matriculated at University College, Oxford on 18 July 1600 aged 17 and was awarded Bachelor on 1 July 1601. He was knighted by James I at Whitehall on 29 April 1607.
As a result, Digges" name was given to Digges Islands, at the mouth of Hudson Bay in Canada, and to Cape Digges, at the easternmost extremity of these islands.
In 1614 Digges was re-elected Member of Parliament for Tewkesbury to the Addled Parliament. He backed the explorations of William Baffin in 1615 and 1616, with several of the same group of "adventurers".
Digges became a gentleman of the privy chamber in 1618. He was named ambassador to Muscovy in 1618-1619 and Special Ambassador to Holland in 1620.
In 1621, he was re-elected Member of Parliament for Tewkesbury.
He was re-elected Member of Parliament for Tewkesbury in 1624, 1625 and 1626. In that parliament, he was active in the impeachment of the Duke of Buckingham during the crisis of 1626 that followed the aborted expedition to Cadiz, when Digges and Archbishop Abbot co-operated to co-ordinate the attacks in the Houses of Lords and Commons. Digges was for a time imprisoned in the Fleet Prison by order of the King, but was released on apologizing to the King, an act that John Eliot was unwilling to perform.
In 1628 Digges was elected Member of Parliament for Kent and sat until 1629 when King Charles decided to rule without parliament for eleven years.
In 1631 Digges became a bencher of Gray"s Inn and was master in chancery from 1631 to 1637. In the same year, he was one of the commission appointed by the Privy Council "to consider how the plantation of Virginia now standeth, and to consider what commodity may be raised in those parts," and in 1634, he was appointed Commissioner for Virginia Tobacco.
In 1638 he was appointed Master of the Rolls until his death in 1639. Digges left a fund in his will that provided, for some 200 years after his death, an annuity of £20 as prize money for races between the men and women of the parish of Chilham.
Digges married Mary Kempe, daughter and co-heir of Sir Thomas Kempe of Olantigh, Kent.
Digges"s son Edward was among the "planters," who emigrated in the 1640s and became Governor of Virginia. Another son, Dudley (c 1612–1643) published a treatise on the Illegality of Subjects taking up Arms against their Sovereigns (1643).
Useless Parliament; Happy Parliament. Addled Parliament; 2nd Parliament of King Charles I]
In 1610 Digges was elected Member of Parliament for the newly enfranchised constituency of Tewkesbury.